Over 50 style

Make a Confident Impression. 8 Simple First Date Outfits

Updated October 30, 2023

First Date Outfits Meant to Flatter You

Are you going to like him? Is he going to like you? Will he measure up to your expectations and vice versa.

A first date may feel waaay outside your comfort zone. It doesn’t matter if you’ve been fixed up on a blind date, met online, or you’re meeting someone  for the first time. It never feels easy.

You could be Jennifer Lopez and looking at marriage number four with your outer shell projecting confidence and sass with a capital S.

But your inner girl is a little more fragile.

Maybe his name is the same as your ex’s.

They may sound like a match but you won’t know until you lock eyes.

Maybe he likes big boobs and you’re not a big boob. You’re crossing your fingers this isn’t a huge waste of time.

Be Confident and Show Off Your Style

The only way to go into a first date is with confidence, reasonable expectations and looking like you couldn’t give a damn. You’re going to be so comfortable and pulled together, he won’t know what hit him.

Even if he’s not the one, or especially if he is the one, you’ll want to feel in control of your game. When we look good, we feel good. That my love is how we get through life and first dates.

Your mission is to become a stealth bomber. Does the bomb care where it goes or who it hits? Heck no. It just IS the bomb. And that’s enough. We’re not saying you’re a destroyer; just own what you are. Don’t make apologies or excuses.

What to Wear on a First Sate.

I’m a very visual person. If you were in front of me I’d know exactly what you’d look good in and what would flatter you. But with a little online magic, we’re going to set you up with some dude-slaying outfits, eight altogether. I know one of them is going to fit you to a T.

I believe the most powerful first date outfit a woman can wear is a dress. Not too slutty, not too office appropriate, but just the right amount of “I know I’m the bomb”.

Flattering First Date Outfits

Just Be the Bomb. Own What You Wear.

Hair, makeup, check. I wouldn’t say go overboard. You know by now what looks good on you. Don’t try to cover up your natural beauty with a ton of lashes or perfume. Honey that will only catch the ones who want superficial. Subtle, don’t give a damn makeup is your goal.

Ditto with your hair. Now I happen to think hair is a pretty big deal. Am I right? You know what to do to make the most of what you’ve got.

Honey, clothes do make a difference, but it’s your inner confidence that’s going to make this first date bearable, survivable and hopefully a blast. Take that “I AM the bomb” attitude with you and you’ll be just fine.

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About Author

With over 30 years in a creative role in advertising and publishing, and a lifetime of journeys between the US and UK, I've created Hipoverfifty for you. I hope my journey and perspective will guide you on yours.